Hydrochloric Acid → 5-Fluoro-1-[(6-fluoro-2-naphthyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 2088985Notes

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:17])[C:5]([C:12]([O:14]CC)=[O:13])=[CH:6][NH:7]2.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([F:38])[CH:34]=2)[CH:29]=1.[OH-].[Li+].Cl>CN(C=O)C>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:17])[C:5]([C:12]([OH:14])=[O:13])=[CH:6][N:7]2[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([F:38])[CH:34]=2)[CH:29]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of ethyl 5-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.050 g, 0.21 mmol), potassium carbonate (0.088 g, 0.64 mmol) and potassium iodide (3 mg, 0.02 mmol) was added the above 2-(bromomethyl)-6-fluoronaphthalene in 1 mL of DMF. The reaction was stirred overnight at 40° C. and 1 mL of a saturated aqueous lithium hydroxide solution was then added to the reaction. After stirring for 30 min, the solution was acidified with 4 N HCl and the product was extracted three times with EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by reverse phase HPLC to provide the 5-fluoro-1-[(6-fluoro-2-naphthyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid which gave a mass ion (ES+) of 366 for M+H+.

Workup

stirringAfter stirring for 30 min
extractionthe product was extracted three times with EtOAc
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-7bed42ae01484949851f3b1a1c04cc91
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436016B2

Reaction notes

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